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Good Quality (4-Bromophenyl)boronic acid丨CAS 5467-74-3
(4-Bromophenyl)boronic acid (CAS 5467-74-3), also known as 4-bromobenzeneboronic acid, is a bifunctional aromatic organoboron compound containing both a boronic acid group and a bromine substituent at the para position of a benzene ring. The presence of these two functional groups provides opportunities for selective molecular construction and further chemical modification. Its boronic acid group is suitable for Suzuki–Miyaura cross-coupling, while the aryl bromide can serve as a second reaction site in subsequent transformations. This makes the compound a useful building block for synthesizing complex aromatic structures, pharmaceutical intermediates, and functional organic materials.
Chemical Identifiers
| InChI | 1S/C6H6BBrO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4,9-10H |
| InChI Key | QBLFZIBJXUQVRF-UHFFFAOYSA-N |
| Smiles | C1=C(C=CC(=C1)Br)B(O)O |
| EC No. | 226-779-9 |
| MDL No. | MFCD00002104 |
| PubChem CID | 79599 |
Applications
Applications in Pharmaceutical and Agrochemical Intermediate Synthesis
(4-Bromophenyl)boronic acid can be used to prepare bromine-containing biaryl and heterobiaryl intermediates for medicinal chemistry research. Its boronic acid functionality enables coupling with suitable aryl or heteroaryl halides, introducing a para-bromophenyl unit into target molecules. The retained bromine substituent provides an additional site for further functionalization, allowing researchers to construct more complex molecular frameworks through sequential synthetic steps. This approach is useful in the preparation of diversified intermediates, lead compound modification, and structure–activity relationship studies during pharmaceutical development.
Applications in Sequential Cross-Coupling Reactions
A distinctive feature of (4-Bromophenyl)boronic acid is the presence of both a boronic acid group and an aryl bromide bond. Under suitable conditions, the boronic acid group can participate in Suzuki–Miyaura coupling with an appropriate organic halide, while the bromine substituent may remain available for a subsequent cross-coupling reaction. This enables stepwise construction of unsymmetrical biaryl and polyaryl structures. The retained bromide can be used in further Suzuki–Miyaura, Sonogashira, or other palladium-catalyzed transformations, depending on the selected reaction partners and conditions. Careful catalyst and reaction-condition selection is important to achieve chemoselectivity and avoid competing reactions involving both functional groups.
Applications in Organic Synthesis and Functional Molecule Development
(4-Bromophenyl)boronic acid is valuable for preparing substituted aromatic compounds with multiple functional groups. Its para-bromine substituent can be retained for later derivatization or used as a handle for introducing alkynyl, aryl, or other functional groups. This flexibility supports the synthesis of complex molecular architectures and provides access to compounds that may be difficult to obtain through single-step transformations. It is particularly useful in research involving biaryl compounds, extended aromatic systems, and multifunctional organic intermediates.
Applications in Organic Electronics and Functional Materials
Brominated aromatic building blocks are frequently used in the preparation of conjugated molecules and advanced organic materials. (4-Bromophenyl)boronic acid can contribute to the construction of extended aromatic structures through sequential coupling reactions. The resulting compounds may be investigated as intermediates for organic semiconductors, optoelectronic molecules, conjugated oligomers, and functional polymers. Its two reactive sites provide opportunities to control molecular architecture and introduce different aromatic units, supporting research into structure–property relationships and the development of materials with tailored electronic or optical characteristics.
